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Para‐Functionalization of N‐Substituted 4‐amino[2.2]paracyclophanes by Regioselective Formylation
Author(s) -
Felder Simon,
Micouin Laurent,
Benedetti Erica
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100288
Subject(s) - formylation , regioselectivity , chemistry , derivatization , combinatorial chemistry , surface modification , amine gas treating , chirality (physics) , aldehyde , planar chirality , catalysis , organic chemistry , enantioselective synthesis , chiral symmetry breaking , high performance liquid chromatography , physics , quantum mechanics , nambu–jona lasinio model , quark
Herein, we report a simple and convenient procedure to prepare para ‐disubstituted [2.2]paracyclophanes in a straightforward manner. Our approach relies on a regioselective formylation of N‐substituted 4‐amino[2.2]paracyclophanes, which allows an easy access to a series of products incorporating a reactive aldehyde function para to the electron‐donating group. These compounds can be engaged in a variety of orthogonal late‐stage derivatization processes involving either the carbonyl group or the amine function, and can serve as precursors to rapidly access more complex paracyclophane derivatives. Control of planar chirality is also possible by performing a kinetic resolution of key racemic intermediates through asymmetric transfer hydrogenation. The formylation can be run on a synthetically useful scale, thus confirming the practical applicability of our method.